The Messy Middle is a guide to "navigating the volatility of new ventures and leading bold creative projects by Scott Belsky, entrepreneur and Chief Product Officer at Adobe. “Creating something from nothing is an unpredictable journey. The first mile births a new idea into existence, and the final mile is all about letting go.” The book argues that the middle stretch is the most important and often the most ignored and misunderstood.

Belsky has a whole section defining culture and how it’s spread through stories. He writes:

Culture is created through the stories your team tells. The term “culture” is casually thrown around as if it can be designed in a conscious way: a cocktail hour here, a foosball table there. But culture is not in any manager’s control. It’s organically formed through the stories your team tells.

The stories a team recalls and shares about itself serve as a continual reminder for everyone of why they’re there and what makes the team special; they reinforce the foundations of a business and the aspirational elements that tie people together...

…[Stories] orient new employees and provide institutional knowledge. Even amid long periods of ambiguity and uncertainty, a healthy culture built on stories provides the context and comfort everyone needs to stick together and keep moving forward.

As a company grows, culture becomes less impacted by everyday stories and is floated on the remnants of the stories that happened early on. Tales from “the beginning” tend to have an outsized impact on the culture as they reflect the core, founding values of why and how this whole thing got started in the first place…Over time, even if the stories themselves are forgotten, the beliefs, values, and nuances of a company’s culture are collectively held by everyone.

If you’re a founder of a project or team, Belsky offers this suggestion:

You need to be present… especially in the early days. You need to recall [the stories] on the right occasions. And you need to let go of the reins and allow the characters on your team to begin making their own. Every team has a few “culture carriers” that are especially good at capturing great stories and retelling them. As the founder of a project of team, take stories seriously.

Bring Your Human to Work, by workplace strategist and business coach Erica Keswin, argues that companies need to focus on relationships. “As human beings, we are built to connect and form relationships. So, it should be no surprise that relationships must also translate into the workplace, where we spend most of our time! Companies that recognize this will retain the most productive, creative, and loyal employees, and invariably seize the competitive edge.”

In the book, Keswin spotlights a great example of intentional culture at Airbnb:

Airbnb’s brand is all about creating a sense of belonging, and not just for their guests and hosts. They actually have a group of employees (10 people in San Francisco and someone in almost every office in the world) whose role it is to take the values off the walls and into the halls. Similar to the role of ground control in an airline, the group takes care of the office environments, events, internal communications, employee recognition, celebrations, and even the design of the office. According to Mark Levy, the former head of employee experience, these people aren’t “forcing fun, they’re reinforcing and supporting how we bring the culture alive.” Levy says, “They do it through pop-up birthday celebrations, anniversaries, or baby showers as well as creative themed events based on holidays or events— whether it’s Pride of the launch of their entry into Cuba.” This is the kind of effort it takes to truly scale culture."

Keswin also spotlights a way of parting gracefully:

“So here you are. You’ve just joined Jellyvision, and we want to talk about the END of your employment here. What’s up with that?"

That is the beginning of the Graceful Leave Policy at Jellyvision, the maker of interactive software. The idea is that each person Jellyvision hires is so valuable, and finding a replacement is so tricky, that out of respect, Jellyvision asks employees to notify the company when they start to look for a new job, apply to school, etc. In exchange for this respect, employees will get the support of Jellyvision in their job search, contacts and introductions, resume assistance, and even prorated compensation.

Talk about transparent!

After an employee shares such wishes with Jellyvision, he or she will continue to be staffed on projects that “make sense” given the timing of the departure (some people have stayed on for more than six months), and employees are expected to work hard until the end. Parting ways is never easy, but at Jellyvision it’s done with the human touch.

In this episode of How I Built This, Guy Raz interviews Stewart Butterfield, founder of Slack. Butterfield talks about how to it's important to get the entire organization aligned to create a good culture. He shares that it’s easy to do this with 8 people, but much harder with hundreds.

Michele Gelfand is a cultural psychologist, and she’s studied how tightly or loosely people adhere to social norms in different cultures. For example: “Why are clocks in Germany so accurate while those in Brazil are frequently wrong? Why is the driver of a Jaguar more likely to run a red light than the driver of a plumber’s van? Across all age groups, family variations, social classes, businesses, states and nationalities, she’s identified a primal pattern that can trigger cooperation or conflict.”

From an organizational culture lens, Gelfand writes about how the merger of Daimler-Benz and Chrysler in 1998 was plagued by a mismatch of a loose culture (American company Chrysler) and a tight culture (German company Daimler).

“In cultural integration workshops at the conjoined company’s headquarters in Stuttgart, American employees were taught German formalities, such as keeping their hands out of their pockets during professional interactions. German members of Daimler’s team felt uncomfortable when their American counterparts called them by their first names, rather than by their title and last name. And while the Germans wanted thick files of prep work and a strict agenda for their team meetings, Americans approached these gatherings as a time to brainstorm and have unstructured conversations.”

Another issue was competing leadership styles. “At Daimler, which revered work formalities, all business decisions came from top executives. By contrast, Chrysler’s executives often granted mid-level managers the ability to oversee their own projects, unconstrained from above.” (Beyond these two companies, Gelfand gives examples of how organizational leaders in loose cultures, such as Israel, go even further, intentionally fostering a culture of disagreement.)

Integrating these two companies was hard work. Daimler could either “compromise or cannibalize,” and it chose to cannibalize. They dispatched German managers to Detroit, and laid off American managers. Unsurprisingly, trust between the two groups plummeted. What followed was 9 years of decline in employee morale and stock price. The two companies split up in 2007. The lesson is: when merging organizations don’t consider cultural compatibility, specifically around tight and loose cultures, they can face huge challenges.

Gelfand also writes about how even within the same industry, different organizations can be tight and loose, and gives an example about IDEO!

“McKinsey and IDEO are both consulting firms, but the former work culture veers tight, while the latter leans loose. This makes sense when we consider their clients: McKinsey’s work tends to include strategy and risk assessments for corporate finance industry and government organizations, while IDEO mainly works on more creative and artistic projects for companies such as Coca-Cola and Apple. McKinsey values a hard-nosed list of company-wide objectives. Unlike IDEO consultants, McKinsey-ites have far more standardized procedures to observe at work. New hires must absorb the infamous “McKinsey way” of doing business in a rigorous training program, learning rules about how to brainstorm as a team member, make client presentations, and follow specific problem-solving steps to break down a business issue. IDEO’s loose company values, on the other hand, urge employees to ‘learn from failure’ and ‘embrace ambiguity.’ At IDEO, self-governing teams aren’t beholden to managers. The relaxed dress code is tied to a more laid-back interpretation of professionalism.”

I loved Jason Fried and David Heinemeier’s first book, Rework. In their new book, they write about how the chaos, anxiety, and stress of the modern workplace is causing employees to burnout. Instead, they encourage organizations to become calm. They share how they’ve done this at their own organization (Basecamp), and how others can follow their lead. Here are a few of my favorite excerpts:

We’re not family:

“Companies love to declare “We’re all family here.” No you’re not. Neither are we at Basecamp. We’re co-workers. That doesn’t mean we don’t care about one another. That doesn’t mean we won’t go out of our way for one another. We do care and we do help. But a family we are not. And neither is your business.

…Whenever executives talk about how their company is really like a big ‘ol family, beware. They’re usually not referring to how the company is going to protect you no matter what or love you unconditionally. You, like healthy families would. Their motive is rather move likely to be a unidirectional form of sacrifice: yours.

…The best companies aren’t families. They’re supporters of families. Allies of families. They’re there to provide healthy, fulfilling work environments so that when workers shut their laptops at a reasonable hour, they’re the best husbands, wives, parents, siblings, and children they can be.”

The trust battery:

“Tobias Lutke, CEO at Shopify, coined the term: “Another concept we talk a lot about is something called the ‘trust battery.’ It’s charged at 50 percent when people are first hired. And then every time you work with someone at the company, the trust battery between the two of you is either charged or discharged, based on things like whether you deliver on what you promise.

The adoption of this term at Basecamp helped us assess work relationships with greater clarity. It removed the natural instinct to evaluate whether someone is ‘right’ about their feelings about another person (which is a nonsense concept to begin with). By measuring the charge on the trust battery, you have to do different things in the future. Only new actions and new attitudes count… A low trust batter is at the core of many personal disputes at work.”

Don’t be the last to know:

“When the boss says ‘My door is always open,’ it’s a cop-out, not an invitation. One that puts the onus of speaking up entirely on employees.

…If the boss really wants to know what’s going on, the answer is embarrassingly obvious: They have to ask! Not vague, self-congratulatory bullshit questions like ‘What can we do even better?’ but the hard ones like ‘What’s something nobody dares to talk about?’ or ‘Is there anything you worked on recently that you wish you could do over?’ Or even more specific ones like ‘What do you think we could have done differently to help Jane succeed?’

Posing real, pointed questions is the only way to convey that it’s safe to provide real answers…. The fact is that the higher you go in an organization, the less you’ll know what it’s really like.”

I loved Jake Knapp’s book Sprint (and have dog-eared many pages as reference) about how to run a one week design sprint. In this article, Rasmus Belter writes about how to run a design sprint while developing a strong team spirit along the way. Even if you’re not running a design sprint, you can steal some of theseteam development exercises to use on your own.